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Published on: June 10, 2021
Photoredox-Catalyzed Radical-Addition/Hemiaminalization Cascade of Cinnamaldehyde: Modular Access to
Jia-Le Yan1, Zhi-Lin Liu1, Hao-Yue Xiang1
1College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. China.
Abstract:
A new photoredox-catalyzed cascade was accomplished by taking advantage of the bifunctional reactivity of bromodifluoroacetamide with cinnamaldehydes, enabling rapid construction of structurally diverse and highly functionalized difluoro-5-hydroxypyrrolidin-2-ones with excellent chemo- and regio-selectivity. Notably, this transformation proceeds a well-designed tandem process involving sequential regioselective radical addition and challenging hemiaminalization. This strategy provides an innovative modular approach to assemble rarely accessed difluoro-γ-hemiaminal heterocyclic scaffolds, which would facilitate further exploration of their pharmaceutical applications.
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The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
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